4.8 Article

MegaStokes BODIPY-triazoles as environmentally sensitive turn-on fluorescent dyes

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CHEMICAL SCIENCE
卷 4, 期 5, 页码 2168-2176

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ROYAL SOC CHEMISTRY
DOI: 10.1039/c3sc22166k

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  1. A*STAR Biomedical Research Council, a Singapore Ministry of Education Academic Research Fund Tier 2 [MOE2010-T2-1-025]
  2. NGS Scholarship
  3. Medical Research Council

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A novel class of triazole-derivatized BODIPY compounds have been synthesized on solid-phase by employing mild reaction conditions based on the copper-catalyzed azide-alkyne cycloaddition. The resulting BODIPY-triazoles exhibited MegaStokes shifts (up to 160 nm) and remarkable environmentally sensitive quantum yield increments that asserted their potential as turn-on fluorescent sensors. Out of a library of 120 compounds, we identified BDC-9 as a fluorescent chemosensor with high sensitivity and remarkable species-selectivity towards human serum albumin. These results validate MegaStokes BODIPY dyes as new fluorophores for the development of environmentally sensitive fluorescent probes.

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